I was meeting Wednesday with a man who’s interested in joining my company as an agent. He had told me about the twists and turns of his own career, and he asked how I had ended up where I am professionally.
I told him about my early successes in journalism. I mentioned owning several small publishing businesses, then becoming a publisher for a newspaper chain — and then spending years as a political consultant. And on and on. I tried to quickly summarize a long story.
“I still haven’t decided what I want to do when I grow up,” I joked.
I didn’t mention the specifics of the many failures in my life. I didn’t talk about the dreams that I’ve given up. And I definitely didn’t talk about the role that luck and chance have played, for both good and bad.
The truth is that I’ve felt lost for much of my life. I started out with a life map that was totally wrong. I trusted cultural training that I didn’t know to question. I set goals that would have made me miserable if I’d achieved them. And the things that now matter most to me would have sounded trivial or inconsequential when I started.
If the 25-year-old David could see where I am now, he would have been dismayed. And if the current version of myself had ended up where my 25-year-old self expected to go, I would be miserable.
My losses and defeats have taught me plenty of important lessons. My wins and successes have felt great to my ego, but they’ve taught me virtually nothing.
Life has been just the opposite of what I expected.

I fear nobody will come with me as I start down a difficult path
Don’t be shocked if insane system produces narcissistic leaders
Freedom lovers, why do so many of you still blindly trust the GOP?
Don’t fret about AI taking over, because software has no taste
If you must be ‘good enough,’ you’ll never start to be yourself
We hate ourselves for needing other people’s approval so much
No matter how ‘defeated’ you are, there’s a way to transform yourself
As I grow and learn, I have to leave more of my ideas behind
We’re all broken, but some of us find meaning in broken partners